Start by preheating your oven to 375°F so it's ready when you need it. While it heats, measure out all your dry ingredients (flour, cocoa, baking soda, baking powder, and salt) into a small bowl and whisk them together to distribute the leavening agents evenly. Bring your egg to room temperature by letting it sit on the counter—this helps it incorporate better into the butter mixture and creates a more cohesive dough.
In a large mixing bowl, beat together the butter, white sugar, and packed brown sugar for 2-3 minutes until light and fluffy. The brown sugar adds moisture and helps create a chewier cookie texture, which is essential for that signature Crumbl cookie quality. This creaming process incorporates air into the mixture, which helps the cookies rise and develop the right texture.
Add the room temperature egg to the creamed butter mixture and beat until fully incorporated, about 30 seconds. Then add the vinegar, red food color, and vanilla, mixing until the color is evenly distributed throughout—you want a consistent red hue with no streaks. Gently fold in the dry ingredient mixture from Step 1 using a spatula or wooden spoon until just combined; don't overmix, as this can lead to tough cookies. I like to mix until I just barely see a few flour streaks, then stop—overmixing is the enemy of tender cookies.
Refrigerate the dough for 15-20 minutes to firm it up and allow the flavors to develop. While the dough chills, line a baking sheet with parchment paper. Once chilled, scoop the dough into 5 large balls (these will be your main cookies) and reserve a small piece (about the size of a walnut) for crumbling later. Press each large dough ball flat onto the prepared baking sheet, spacing them about 3 inches apart to allow for spreading.
Bake the pressed cookie dough at 375°F for 10-11 minutes—they should be set on the edges but still slightly soft in the center when you remove them from the oven. The small reserved piece of dough can go on the baking sheet during the last 5-6 minutes of baking so it's ready to crumble. Let all cookies cool on the baking sheet for 5 minutes to firm up slightly, then transfer to a wire rack to cool completely.
While the cookies cool, prepare the frosting by beating together the softened butter and cream cheese until smooth and creamy, about 1-2 minutes. Gradually add the sifted powdered sugar (sifting removes lumps for a smooth frosting texture) and vanilla, beating until light and fluffy. I prefer to use Philadelphia full-fat cream cheese because it creates a thicker, richer frosting that pipes beautifully and holds its shape on the cookie.
Once the cookies are completely cooled, transfer the frosting to a piping bag fitted with your desired tip and pipe a generous swirl onto each cookie. Crumble the small baked cookie piece from Step 5 over the top of each frosted cookie to add texture and enhance that authentic Crumbl appearance. Let the frosting set for a few minutes before serving.